


The One Where They Failed Multiple Times

by HolyFuckingHell



Series: Cas's List [9]
Category: Supernatural
Genre: Anal Sex, Blow Jobs, Boss Kink, Bottom Dean Winchester, Cowboy Kink, Cowboys, Doctor Kink, Fluff, Fluff and Smut, Hand Jobs, M/M, Oral Sex, Roleplay, Sex, Smut, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2020-10-22
Updated: 2020-10-22
Packaged: 2021-03-08 22:14:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,313
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27143665
Author URL: https://archiveofourown.org/users/HolyFuckingHell/pseuds/HolyFuckingHell
Summary: Roleplaying is awkward no matter how much Dean wants to do it. Also, he's kinda bad at it. Cas, surprisingly, is amazing at it. They try a few different scenarios, most ending in sex... There was that one time, but mostly it ends with sex. Roleplay though, they can't seem to get it right. Eventually they figure out something that might work.
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Series: Cas's List [9]
Series URL: https://archiveofourown.org/series/1887445
Comments: 9
Kudos: 90





	The One Where They Failed Multiple Times

**Author's Note:**

> What is this? Part nine? Rock and freakin role. Sorry, it's been taking me so long to upload these, whoops.
> 
> Also, there's a part when they're cowboys I want to clear up. I really like western movies so I've heard a lot of these phrases. All aboard kinda is like saying is anybody home when someones being, like, dumb or something. And a lick and a promise is to do a job in its entirety, but not very good. 
> 
> Good luck.

The first time they tried it, it didn’t really work. Dean spent a while deciding what he wanted to do most. Cas told him that since he couldn’t decide, they could try it multiple times, it doesn’t have to be a one-time thing. But after lots of time and thinking, Dean told Cas that he wanted to roleplay as a cowboy and a painted lady, also known as an old-timey, wild west prostitute. Dean wanted to be the prostitute. 

Basically, the plan was simple. Cas would be the cowboy and he’d walk into the ‘whore house’ that Dean was working at and Dean would do everything Cas asked him to do because he’s a good whore who makes good money. 

Dean gathers Cas a pair of his tighter-fitting jeans in hopes they will work for him, a shirt that he thinks will work for this outfit, and a hat. “Don’t ask me why I have this stuff.”

“I know why you have these things, Dean, but what I don’t understand is why you have extra… In my size,” Cas explains, holding out his arms for Dean to pass the pile of clothes.

“I remember saying  _ ‘don’t ask.’” _

“I didn’t ask.”

“Okay,” Dean pushes Cas, “Go change then come back.” Dean got Sam and Jack to leave and the best part about it is Dean genuinely had a reason for them to go so there is no way they could know for sure that Dean is excusing them for sex stuff. 

Cas disappears out the door and Dean excitedly takes off his shirt as quickly as he can. Dean didn’t really know what a male prostitute would wear in this time and region, but he’d imagine they’d be shirtless. Dean is wearing jeans and a hat. He couldn’t decide what underwear to wear so he didn’t wear any. 

Dean sits, waiting on the bed for Cas. He hears footsteps and the excitement makes him jump. The knob turns and the door slowly creaks open and there stands Cas looking rugged and hot as hell. No, hotter than hell, and Dean means it. “Howdy.”

“Holy fuck,” Dean breathes out, visibly shaking with excitement at Cas dressed as a cowboy.  _ His  _ Cas.  _ His  _ Cas is dressed like a cowboy! He can’t believe it. 

Cas squints at him, giving him a quick look up and down. “That’s blasphemous,  _ boy _ .” In most, if not all, the western movies Cas has seen with Dean, the cowboys call others ‘boy.’ Dean shakes his head quickly like his brain is an etch-a-sketch and he’s trying to clear his mind and refocus. “I do hope I’m in the right place…”

“That de-,” Dean swallows, “That depends.”  _ Fuck. _ He’s just so excited. “What are you looking for?”

“Hopefully, someone like yourself,” Cas grins, “If you're willing more than just a lick and a promise… I’m feeling real…  _ needy. _ ”

“Fuck, Cas, this isn’t working!” Dean bites his lip, hard in his jeans already.”

“Are you all aboard, partner?” Cas asks, still pretending to be a cowboy for Dean. “What seems to be the problem? What’s not workin’ for ya?” 

“No, it’s just working too well.” Dean starts kissing Cas intensely and their hats push together.

“Woah, you’re friendly,” Cas says between kisses, “You kiss all your customers this way?”

“Seriously, Cas, just fuck me. I can’t do it. Too hot,” Dean pants.

“I didn’t want to be rude,” Cas says normally, “But I thought doing your most intense fantasy first was not going to work.” Cas picks Dean up and drops him on the bed and then starts taking off his clothes.

“Leave the hat!” Dean says. 

“As you wish,” Cas grins. Next, he starts undoing Dean’s pants and pulling them off. “You’re not wearing underwear,” Cas says pleasantly surprised with a small blush. 

“I was supposed to be a whore.”

“Is that why?” Cas gets them finally both naked. 

“I’m a horny bastard, that’s why. Please fuck me you sexy fucking cowboy with your deep fucking voice.”

“Blasphemy!” Cas jokes.

“Shut up!” Dean jokes back. 

Their second time trying it was worse than the first. Dean, learning from his mistake, picked something he thought was less hot. Still hot, of course, just less hot. One extreme to… less extreme? He guesses? Not realizing it, Dean overcorrected. Dean proposed a librarian and a loud, out-of-line customer.

Basically, the plan was simple. Dean would be the customer, or student, or whatever and he’d make a mess and be too loud for a library so Cas, as the librarian would have to ‘deal with him’ and Dean would do everything Cas asked him to do because he’s under the mercy of Cas and whatever punishment he sees fit for the trouble he’s caused.

Dean figures Cas can wear his normal clothes just nix the coat and jacket. If he had a sweater for Cas to put over his dress shirt and tie he’d have him wear one, but unfortunately he doesn’t. Dean just tells him to roll his sleeves up. 

Cas looks good, but then again, he always looks good like this. Like he was previously put together but is now slightly disheveled. It’s nice. 

This time, Sam and Jack are both in the bunker. It’s mid-afternoon so they are both doing their own things though Cas is fairly sure Jack is in the library and Sam is watching TV which is rare for Sam to do on his own. 

Here’s where the ‘worse’ part comes in. Dean started giggling. Then Cas said something and Dean started nervously laughing. Then hysterically laughing.

Dean truly, honestly was  _ not _ laughing at Cas. He was supposed to say something back to Cas, in character, because that’s how roleplay works, but he couldn’t get any words out. And hot, librarian Cas was staring down at him, waiting. Dean felt silly. Then he thought about what they were doing, or rather,  _ trying to do _ , and he thought it was ridiculous. So, laughing. 

Dean laughed so hard his sides started to hurt. Cas watched him, unamused. Dean sat on the bed, doubling over in laughter. Cas  _ hates _ when Dean laughs like this... when Cas thinks it’s at him. Ever since the whole ‘kissing thing’ from the start. Cas rolls down his sleeves, “Alright,” he turns around and heads for the door, “We aren’t doing this one,” He grumbles frustratedly, picking up his coat and jacket and putting them back on. 

“Wait, Cas!” Dean’s laughing quiets down. Cas stops with his hand on the doorknob. “I’m sorry I’ll-” Dean forces back a laugh “I’ll stop!” Dean laughs again. He can’t stop. 

“That’s what I thought,” Cas opens the door. 

“No,” Dean giggles. “Come back and we’ll have  _ regular _ sex.”

“No, you’ve killed my mood. Maybe later.”

“Who’s gonna fuck me of not you?” Dean says sweetly. 

“Fuck yourself, Dean. You have dildos and vibrators for that.” Cas disappears down the hallway. 

“Damn it,” Dean giggles to himself. He’s obviously not gonna do that right now, it’s insensitive, right? No matter- Dean’s eyes drift to the drawer- No matter how tempting it is. 

Dean rolls his eyes and gets up off the bed to go be with Cas. 

Later they talked about it again. Football player and a cheerleader.

Basically, the plan was simple. Cas would be the football player and he’d be hosting a house party after the game and Dean would be a cheerleader attending and they would sneak off to Cas’s room and Dean would do everything Cas asked him to do because he played really well and deserves a reward. 

Dean has sweat pants and tee shirts that Cas could have worn, and Dean has a mini skirt,  _ for reasons, _ and he could have worn that.  _ Could have. _ If they ever tried it. Dean was able to talk about it and explain it to Cas fairly well. What he could  _ not _ do was talk about  _ actually doing it. _ They tried to plan when they were going to do it, but Dean wouldn’t stop laughing. 

Turns out Dean is a bit less comfortable than he thought. He does try again though. Dean thinks this one will be easier because it’s not a lot of acting, they’ve done things like this before. Dean wanted to be pirates.

Basically, the plan was simple. Cas would be the captain Dean could be part of his crew. It could start off as Dean wanting to become a pirate and join them but he doesn’t really have any skills so the Captain says no. Then Dean could offer to prove himself useful in… other ways. Dean would do everything Cas asked him to do because his job on the ship was to keep Cas taken care of. 

Cas is pleasantly surprised that Dean seems to actually get this one. But really, it works for all of like, six or seven minutes. They decided in the moment that Dean should be tied up to the bed for this which Dean thinks is exciting. Cas talks to him in character as he gets Dean’s hands tied before he moves onto his feet. 

“Ah, Cas?” Dean says forcing back laughs with most of his focus and all his might. 

“That's _ captain, _ ” Cas growls, finishing the ties to one of his feet. 

“I don’t think I want to be pirates anymore…” He smiles, still successfully holding back laughter. 

“You wish to quit my crew?” Cas squints at him. 

Dean swallows down a chuckle. “Cas, I can’t roleplay, I’m bad at it.”

Cas drops the rope, leaving just one of Dean’s legs unattached. He climbs onto the bed and lays flat on Dean. “Why do you think you’re bad at it?”

“You think I’m good at it?” Dean says giggling. 

“No, you’re awful at it.” Dean huffs, sounding offended. “What I am asking is why?” Dean rolls his eyes. “Well when you do it, you do it well. When you start laughing and you stop doing it, then you’re bad,” Cas defends. “Why can’t you do it?”

“I feel,” Dean chuckles, “Kinda stupid… it’s awkward.” 

“The awkwardness will go away if you push through…” Cas says. “We don’t have to do it if you don’t want to, it was just an idea.” 

“Yeah,” Dean huffs, “An idea that I  _ like _ and want to do!”

“Then we can keep trying.”

“I’m not laughing  _ at you _ , you know that right?”

“I realized that eventually. You are laughing because you are awkward and uncomfortable.”

“You think I’m awkward?” Dean says dimly.

“Not in general. In general, you are rather charming and suave.” Dean blushes. “I’m sure if you really want to do this we can figure out a way.” Cas cuddles into Dean. 

“Cas,” Dean says to get his attention. “I’m still,” He chuckles, “I’m still tied up, man.”

“Oh,” Cas says sitting up. “Do you want me to untie you?”

“Uhh,” Dean shrugs, “No, I actually would rather you take off your pants and ride me like you were going to do before…”

Cas smiles as he gets up to take off his pants. “How did you know that was what I was going to do?”

Dean smiles, “Just a hunch.”

Their continuous efforts continue. Dean tries to really psych himself out before they do it again. 

Basically, the plan was simple. Cas would be the boss, a strict and hard-ass boss actually, and Dean would work for him. Maybe during breaks, or after shifts when everybody goes home, Cas could call Dean into his office and they would… ‘ _ work.’ _ Dean would do everything Cas asked him to do because Cas is the boss and Dean is a hard worker who loves his ‘benefits.’

Dean thinks it could work out pretty easily. Cas already dresses like a man of business and Dean has nice clothes he can put on. They already talked about doing it but haven’t decided when. 

Someday after that, Sam and Jack are out of the bunker because it’s their turn to go grocery shopping. Cas is in the library reading and Dean figures it’s the perfect time to just kind of spring this on him. He puts on slacks and a nice dress shirt with a yellow tie, but no shoes. He  _ did _ put on dress socks though. 

He walks into the library and sees Cas sitting at the table. Cas looks up, “Hello, Mister…” Dean drags the word ‘mister’ out because he didn’t really think this through. Cas hasn’t got a last name. Dean makes a face like he is about to laugh but manages to stop it. Cas squints at him and tilts his head. “...Bossman.” Dean closes his eyes and his mouth goes straight-lined. He lets out one tiny little chuckle then opens his eyes again. He’s smiling a lot, already embarrassed. “You wanted to… meet with me?”

“Yes,” Cas seemed to understand though because he immediately gets into it. He closes his book and stands up, “I’m glad you got the message,” Cas gestures to the chair opposite him at the table. “Please have a seat, Mister Winchester.”Dean smiles and sits down, as he does, Cas sits down too. 

“I think you’ve proven yourself to be a…  _ hard _ worker,” Dean finds Cas’s emphasis on the word ‘hard’ kind of hot. “You do  _ a lot _ for this company.”

“Thank you,” Dean replies, “If there’s anything else I can do,” Dean slides his foot over to Cas’s, “To go that extra mile,” Dean runs his foot up Cas’s leg and Cas raises an eyebrow at him. “Please let me know,” Dean gulps. 

“A few things come to mind, as long as you’re not afraid to get your hands dirty…” Cas says deeply in the voice he knows Dean likes. “Based on your previous work, I know that you are _very thorough_. Tell me, Mister Winchester, do you have any _special_ _skills_ that you have yet to… _display_?”

Dean’s heart beats faster and Cas can hear his breath hitch and speed up. “I would be more than happy to show you,” Dean starts to break, “My skills are,” Dean continues working up and down Cas’s leg slowly. “A bit unorthodox but they  _ get the job done _ .” They stare at each other for a brief moment before Dean spontaneously bursts into laughter. “Cas!” Dean shouts, “I can’t do this,” He laughs. 

“You were doing so well!” Cas stands up and says desperately. Cas whines then says “I wanted you to kneel under the table and-”

“Suck your dick,” Dean finishes for him. “Yeah, I thought about it too…”

Cas sighs, “Yes, I was about to suggest it!”

“Fuck!” Dean’s laughter calms down and he slouches back in the chair casually. Cas smiles at him and sits back down. “I feel stupid. I feel stupid when we play pretend.”

“I don’t understand, you and Sam ‘play pretend,’” Cas does finger quotes, “Every time you have to pose as officials. It’s the same!”

“It’s not the same!” Dean chuckles. “It’s totally different! I just don’t wanna look stupid when we do this!” Dean giggles. 

“Look stupid to who?” Cas asks seriously, “It’s just us.”

“Yeah but you’re so good at it and I’m just,” Dean pauses, “ _ not _ .”

“Just keep going! Be confident! I feel like the only way to resolve your feelings of foolishness is to continue through them!”

Dean chuckles and shakes his head. “Cas, I can’t.” He laughs. “Not this at least. Remember when I called you ‘Mister Bossman?’ I can’t get past that.”

Cas will admit it was a bit peculiar but for the purposes of this conversation he says, “That was great, on-the-spot, ad-libbing improvisions, Dean.”

“No,” Dean giggles, “It was dumb.”

“I liked it!” Cas claims. 

“No, you didn’t,” Dean rolls his eyes. 

“Well, I like you. And you looked very attractive leaning against the threshold and babbling as you tried to figure out what to say to me.”

“No way that was attractive but I like that you will say anything to get into my pants right now. Game respects game.” Dean winks at him. “Now, please carry me bride style into our room and do me while we kiss as much as possible.”

Cas gets up immediately, not saying anything at the fact that Dean called it ‘their room.’ “So we are giving up on this one?” 

Dean smiles as Cas bends down and lifts him up off his seat effortlessly. “For now.”

After that fun little break and two more ‘breaks’ after that, Cas turns to an  _ exhausted _ Dean and suggests, “Maybe it would be better if we role-played a scene from a show or movie that you enjoy…”

“Why?”

“Because then you wouldn’t have to feel strange about any phrases or actions you make up because you will essentially be following guidelines…”

“Okay,” Dean sounds intrigued, “Okay, that sounds like it could be fun!”

“Yes, good! And you can take your time thinking about what scene you want to do. Then tell me so I can watch it. Then we can do it. Does that sound alright?”

“It sounds awesome. I already know which one I want to do.”

“That was quick,” Cas comments.

“Yep! You’re gonna be Don Draper and I’m gonna be Sylvia Rosen! It’s from Mad Men. I’ll show you what I’m talking about later,” Dean yawns.

“Are you going to fall asleep? It’s the afternoon.”

“No, just wanna lay here a little longer.” Dean yawns again, “Maybe a quick nap, I don’t know.”

This is the last time they tried roleplaying. It didn’t work out as planned, but that doesn’t mean it didn’t work. 

Basically, the plan was simple. Cas was going to be reenacting a scene from Mad Men with Dean. Cas is going to be Don Draper, sitting in his chair and ordering around Sylvia Rosen, played by Dean, to do all kinds of sexy things for him. Dean would do everything Cas asked him to do because that’s how it happened in the show. 

Cas is wearing his suit, no coat, no shoes, just like the show, and he’s sitting in Dean’s desk chair. In the show, Sylvia was mostly dressed, then got  _ undressed  _ when Don told her to, but Dean wanted to look sexily disheveled so he’s wearing his most flattering briefs and a dress shirt with the cuffs undone. 

Dean walks in and Cas says the simple word, “Sit,” Commandingly so Dean walks over to the bed to sit down. “Not on the bed,” Cas says before Dean meets the bed. “On the desk,” Cas eyes him. 

Dean smiles and walks over to the desk as casually as possible. He sits down and looks at Cas, “Aren’t you going to come over here?” He says quietly. 

Cas watches him, “No.” Then Dean starts hysterically laughing and apologizing incessantly. Cas gets up in a huff and walks over to Dean, standing between his spread legs, getting close so Dean thinks Cas is going to kiss him. “What happened?”

“I felt silly again,” Dean confesses, low and quiet, leaning in slightly to kiss Cas but Cas leans away slightly to stop him. 

“If you want the truth,” Cas gravels, “I feel silly when I do this too…”

“You do?” Dean says, shocked. 

“Yes,” Cas nods slightly, “It is new and different so it is normal to feel that way. I can work through it though.” It does help Dean a little to know that Cas feels goofy like he does. “I think you can too…”

“Maybe…” 

“Do you want to try role-playing again? You can say no and I can perform some oral stimulation to your penis here and now instead…” Cas says this to relieve Dean of any pressure he feels to say yes. 

“We can try again,” Dean gulps, “I don’t think I can be Sylvia though…” 

“That’s okay,” Cas whispers, leaning almost all the way into Dean’s lips, “We can try something else,” Cas rubs his hands up Dean’s thighs and slides his fingers under the hem of his briefs. 

“What did you have in mind?” Dean says, raising an eyebrow. 

Cas starts unbuttoning Dean’s shirt, “You like doctors…” He comments. He gets Dean’s shirt open then tugs on it, drawing Dean right almost against his lips. So close you probably couldn’t slide paper between the space. “I’ll be your doctor.” Cas kisses Dean for a moment before pushing him away. 

“Am I you’re patient?” Dean asks. Cas nods. “Okay, but if you make  _ one _ joke about a ‘prostate exam’ I’m going to kick you.”

“I may need to find yours though, for the sake of health,” Cas smiles. “Get on the table,” Cas points to the bed. Dean walks over, dropping his shirt to the floor and climbing on the bed. 

Basically, the plan is as simple as it can be. Cas is the doctor, Dean is the patient. Dean would do everything Cas asked him to do because Cas is the doctor, and that’s how it works. 

“Unfortunately,” Cas says, “This check-up may take some time. I have to be very thorough…” Dean smirks at him, “Lay back, please.” Cas puts his hand over Dean’s chest and gets distracted, just feeling and listening to Dean’s heart. Once Cas realizes he’s distracted he zones back in. He moves his hand slowly to Dean’s nipple and circles a finger around it. “I have to do a series of tests to see how responsive your body is…”

“Well, I’ve been told that I am pretty sensitive,” Dean smiles. 

Cas pinches gently on Dean’s nipple and Dean lets out a soft sigh. “So far you seem to be very receptive, whoever told you that is correct. It must have been someone very observant and intelligent…” Cas plays with the other nipple now. 

“Yes,” Dean giggles, “It was.”

Cas slowly glides his hand down Dean’s chest and starts feeling above Dean’s waistline on his underwear. “Very good,” Cas notes, looking at the growing bulge in Dean’s underpants. “Very impressionable…” Cas pulls his hand away, “Now you are going to have to take off your underwear,” Cas says pretty professionally. Dean starts giggling and this time not because he found something amusing. Cas has been through this enough times to know what this kind of giggling means. “It is normal to feel uncomfortable about this,” Cas says to Dean in character as his doctor but also as himself reminding Dean he can do this. “It’s understandable.”

Dean nods and slowly takes his underwear off. “I’ll shake the feeling,” Dean says half-confidently as he gets resituated. 

Cas wraps his hand around Dean’s dick firmly and strokes impossibly slow. Dean reaches over and touches Cas over his pants when Cas grabs his wrist. “Sir, that is inappropriate,” Cas moves his hand back to the bed, “I will ask that you refrain.”

“Sorry, Doc,” Dean says, “You were touching mine so I figured I could touch yours,” Dean smirks. 

“It’s my job to touch your penis,” Cas comments and walks over to Dean’s drawer, pulling it open and getting lube. 

“Is it also your job to make it feel this good?” Dean says and then feels a bit awkward about it. 

“Consider it as a perk,” Cas says, rubbing Dean’s dick down with lube before he continues stroking. Dean’s toes curl and he lets out a whine, closing his eyes and moving slightly into Cas’s hand. “You’re doing surprisingly well,” Cas says.

“Why,” Dean’s voice breaks, “Why ‘surprisingly?’”

“You are responding correctly but you are not yet out of control,” Cas says plainly. 

“ _ ‘Yet?’”  _ Dean grunts.

Cas ignores his half-constructed question, “Lubricant makes the next step more pleasant,” Cas steps away from the side of the bed and moves to the end of it. “If you would please move to the edge,” Cas asks.

Dean scoots down quickly wanting Cas to just touch him again. “Next step?” Dean asks, hoping the next step is what he thinks it is. 

Cas guides Dean to move his legs further apart and to bend his knees. Cas slides in two lubed up fingers and immediately presses it into Dean’s prostate… Much to the surprise of Dean. His hips jerk. “Woah, how did you-?” Cas does it again, “Hah,” Dean whines, “How are you doing that?”

“It’s part of my job,” Cas smirks at Dean, pleasantly surprised that Dean reacted the way he did. Cas starts getting him open. Dean moans. Cas continues on ruthlessly. He adds a third finger and Dean gets louder as the fingering gets rougher. Precome started beading at the head of Dean’s dick ages ago. Cas watches as Dean slowly falls apart. Dean is close to coming, like really close, Cas can tell. That’s when Cas pulls his fingers out. “You appear to be of perfect health,” Cas smirks at him.

Dean looks up at Cas confused and panting and desperate. “Are you- Are you sure? You may need to check again…”

“I’m sure!” Cas cheers. “It’s been a pleasure seeing you today…” Cas lowers his voice, “You  _ are _ my most attractive patient.”

“And  _ you _ are my most attractive doctor… Wish I could stay…” Dean gulps and hopes that’s where Cas is going with this. Surely they can’t be done.

“Well,” Cas says, “If you’re interested in staying…” Cas says suggestively, “You are my last appointment for today…”

“I’m interested…” Dean pants.

Cas starts taking off his tie in the slow, careful way that Dean loves and can’t stand, “Perhaps there is something I missed that I should get a better look at…”

“You didn’t even check my lips,” Dean plays. “They definitely need to be examined.”

“I know the procedure for that,” Cas gets his shirt off and climbs over Dean. 

“I’ve been told they’re soft.”

Cas kisses him for a bit, “I can confirm that. They feel exceptionally nice.”

“Yeah, you think that feels good, you should feel them against your-” Cas cuts him off by kissing him again and grinding into him. Dean groans. “Cah-” Dean catches, “Uh, Doctor! Could you maybe check again what you were checking before?” Dean points down.

“Ah,” Cas says and suddenly the rest of his clothes are gone. He stands up at the end of the bed again. “There  _ is _ a different method for it that I can try. It’s very effective.” Cas picks up the lube again and rubs it on his dick. 

“Very effective,” Dean pants. Cas holds Dean’s legs, right on the undersides of his knees as he slides gently into Dean, “Hah…  _ very effective,”  _ Dean grunts. 

“Of course,” Cas grunts, “I’m good at what I do.”

“Hell fucking yeah you are.” Cas begins thrusting at a steady pace. He did all this on purpose to give Dean some time to cool off,  _ which worked _ . Before this, Dean was on the edge of coming, now he has calmed down… but only a little bit because while Cas did give him time, he didn’t give him much. 

Usually, Cas has a plan but this time he wasn’t sure. While he was fingering Dean he was sure he wanted Dean to come off from that, but towards the end, he changed his mind. His dick, he wanted Dean coming off of his dick, hence the sudden wrapping up of their ‘appointment.’ Cas only hoped Dean would do something to continue it. He figured his sex-addled brain would do something, but having said that, Dean when it comes to roleplaying was a bit unpredictable. 

“You are doing so good,” Cas praises as he drives smoothly in and out. Dean squeaks, covering his mouth with his wrist to try and keep himself at least somewhat quiet. “I’m going to speed up now and see how you respond to that.” Cas speeds up and Dean’s hips jerk naturally. 

“Fuck,” Dean curses, biting his bottom lip. 

“You are close to ejaculating,” Cas states as a fact.

Dean blushes. “Sorry,” He squeaks. He wants to defend himself just a little. It’s just that before, Cas had him less than seconds away from blowing it and it didn’t fully wear off. Unfortunately, he can’t seem to speak clearly and he just moans. 

“The point is for you to ejaculate,” Cas reminds, “Apologizing is not necessary.” Dean moans again. He’s definitely coming way too fast. Cas is absolutely nowhere near coming. On top of that, Dean doesn’t think there is anything extra he can do for Cas in this moment to help him along. And  _ fuck  _ he is close. “Now is the appropriate time for you to ejaculate, Mister Winchester,” Cas says way too nonchalantly for a guy screwing another guy. 

Dean still tries to hold out though. Cas, seeing this, takes his hand to Dean’s dick and starts stroking again which is unfair, to say the least. Dean moans. He’s shocked, but mostly he just can’t take it. “Oh, Doctor!” Dean shouts more high pitched than he would have liked to as he comes.

Cas grins, not knowing he would like hearing that as much as he did. Cas pulls out, “Fantastic,” He says as he climbs on the bed next to Dean.

Dean tries catching his breath, “You bastard, You couldn’t let me last a little bit longer, could you?”

“You appeared to be ready,” Cas shrugs, laying down.

“No, wait,” Dean pants, “Don’t lay down… straddle me!” Dean proposes. 

“Straddle you?” Cas sits up. 

“Yeah, like, right here,” Dean pats the upper part of his stomach area and gazes excitedly as Cas climbs onto him. “Yeah…” Dean smiles and he moves his hand to Cas’s dick. “I hate when you don’t come.”

“You  _ hate _ it?” Cas questions. “That is such a strong emotion to feel for something as menial as it is.”

“It’s not menial, Cas! I come  _ literally _ every time and you come… like… half the time.” Dean strokes faster. 

“You shouldn’t worry about that, Dean. If I want to ejaculate I will! You should feel relieved in the fact that if I want to I can just edge you to keep you from ejaculating too soon.”

“Well, I  _ do _ worry about it,” Dean does the thing with his thumb that Cas likes and Cas groans, “And I still hate it when you don’t come.”

“I’ll respect your feelings then. I do hope that you might feel different eventually though.” Cas swallows, “I enjoy being with you just as much,” Cas groans again. 

“With me? Or like,  _ with me _ with me?”

“ _ With you _ with you!” Cas moans. “As in intercourse. Though I do also enjoy your company, of course. That’s not the point. Do you understand what I’m saying though?”

“I think so,” Dean pants again. He’s almost got his breathing back to normal. “You like having sex as much as you like coming from it.”

“That is a very simplified version, but yes,” Cas’s voice breaks slightly at the end. “Please put more pressure… If you can,” Cas says softly.

Dean doesn’t really know what Cas means by ‘more pressure,’ but he does hold tighter and that seems to do the trick. It’s not much later until Cas is coming, quiet as always, and with a respectful warning. “Ooo,” Dean drags a finger through Cas’s come which landed on his chest. “Fuck, that’s a lot of come.” Dean brings his finger to his mouth and licks the come off of it. 

“I really enjoy it when you do that,” Cas mentions with a smile.

Dean nods as he slowly does it again with a smirk on his face, looking right at Cas. “I know…” 

Cas smiles.

Dean never knows where their clothes go when Cas poofs them away but they usually just poof back when Cas wants them. “Can I see the catalog again?” Dean asks Cas. It looks like Cas picks up his coat off the bed but Dean knows Cas’s coat wasn’t there before. Cas fiddles around with it until he reaches into the pocket and pulls out the list for Dean and passes it to him. Dean looks at it for a moment before looking up at Cas, who is still sitting on him. “Cas, can I ask you a question?”

“Of course. You can ask me anything.”

Dean’s eyes fall back to the bottom of the paper where there are now five scribbles. Five  _ illegible _ scribbles. “What do you keep writing at the bottom?”

Cas holds the top of the paper to take it back and Dean lets go from fear of ripping it. Cas very gently and slowly tears a strip off the bottom and hands it back to Dean. “Now there is nothing.”

Dean stares up at Cas with his mouth hanging open, completely dumbfounded. “Cas,” Dean says softly, “I thought you said I could ask you anything.”

“You  _ can _ ask me anything!” Cas retorts. 

Dean sighs, knowing that it’s probably a lost cause. 

“What is feltching?” 

“I’m still not going to tell you,” Cas half smirks at him. 

“I thought so… I still just wanted to try.”

“You haven’t looked it up?” Cas asks shocked.

“ _ You told me not to. _ ” 

“Yes I did, I’m impressed you have fought through temptation.”

“Thanks?” Dean giggles. Cas reaches down and starts playing with both of Dean’s nipples as Dean reads through the list again. You would think he was trying to memorize it. “How come we haven’t had sex on my car yet?”

“That is your fault,” Cas says plainly.

“ _ My fault?!” _ Dean laughs. “How?!”

“Since it is up to you to decide when we do that, it is your fault we have yet to do it.”

“I didn’t know it was on me to decide!”

“It is  _ your _ car. All you have to do is ask.”

“That would’ve been nice to know before, but I’m glad I know now.”

Cas moves until he is laying down next to Dean. Dean shuffles up on the bed until he’s at Cas’s level and his legs are no longer dangling off.

“Cas,” Dean swallows. He still finds it hard to be real sometimes. Especially after something as goofy as what they just did. “You know you can tell me anything, right?”

“Yes, Dean, I know,” Cas forces a smile. “Don’t think about it too much,” Cas says with a slight fear because he knows if Dean wants to, he can figure it out again.

At this point, Dean is actually frustrated that Cas won't tell him.  _ Five times. _ Cas has written whatever this is  _ five times. _ That’s so many times! And he won’t even tell him! Cas obviously wants to do this. Dean can’t believe Cas ripped the bottom off the paper. But, Dean knows Cas is sensitive about whatever it is so he tries to be respectful. 

“I am waiting,” Cas says, turning his head to look at Dean.

“Waiting for… what?” Dean looks back at him. Cas raises an eyebrow and says nothing. “Umm… I liked it a lot. I like that you’re so good at roleplay, I wasn't expecting that.”

“You weren’t expecting it?” Cas says, sounding offended.

“Cas, com’ on. Remember when you were ‘bad cop?’” 

Cas thinks back. “I did good!”

“You literally, I kid you not,  _ screamed _ at the lady ‘Why did you kill your husband.’”

“Yes,” Cas defends, “That was a good example of a bad cop. So of course I’m exceptional at roleplay.”

“You’re right Cas,” Dean giggles, “My bad.”

“So then how was your orgasm?”

“Why do you always ask this? You already know it was awesome and that I liked it.”

“I like to hear you say it,” Cas says seriously. 

“Cas,” Dean starts, “You give me the best orgasms and I like them very much. This one was-” Dean is about to say ‘awesome’ when he interrupts himself distractedly with a question. “Hey, did you plan on having me… I mean you probably did… You always have a plan so… Nevermind, just-”

“Well, my original plan was to make you come by stimulating you with just my fingers but I decided in the moment to use my penis instead.”

Dean’s eyes blow open wide. There is no need for Cas’s exact corrects terms to make Dean aroused but they do anyway. “Ohh, I was right then…” Dean says softly. 

“I’m surprised you noticed,” Cas says. 

“Is that an insult?” 

“No.” Cas moves his hand to Dean’s dick.

Dean winces, “Cas, I’m still a little too sensitive for that right now.”

“Then why are you thinking about me inside of you again?”

“Are you reading my mind?” Dean asks seriously. 

Cas laughs, “No, I like to think that I just know you very well. Obviously, I do.”

“It’s your fault! You started talking about your dick in my ass…” Dean accuses. Cas smiles. “You know I love when,” Dean laughs through the awkwardness he feels because he knows Cas will enjoy hearing him say it. And if he’s being honest he also wants to say it again. “You put your dick,” Dean chuckles, “In my ass.”

“What about  _ your _ dick in  _ my _ ass?” Cas asks way too seriously with innocent eye contact. 

“I can go both ways,” Dean nods and gulps. 

“Would you like to? We have some more time if you want. That is, of course, after your-”

“Yeah! Okay, yeah!” Dean says, wiggling closer to Cas. “Turn over,” Dean says to Cas as he sits up and kneels on the bed. “I’ll finger you until I’m ready.”

“That could be a while,” Cas turns over, “Are you sure?”

“Yeah, it’ll be fun! And I’m sure you can take it,” Dean laughs to himself which makes Cas smile. “Where’d the lube go?” Dean glances around but stops when Cas passes it to him.

“Can you please put the list back into my coat pocket before you start?” Cas says calmly. 

“Sure,” Dean says, doing the chore quickly. “You and your priorities” Dean rolls his eyes, feeling very excited for a man who does this somewhat often. 

**Author's Note:**

> This was weird to write, lol. Also, I kept switching tenses and I couldn't fix it so I gave up. RIP.
> 
> Let me know what y'all think! Any ideas too! Comment please! I'm begging!!


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